1,2-Dichloroethane → HCID 67174408, compound

HRID 1256174Notes

Reaction equation

HRID 1256174 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.O/[N:27]=[C:28](/[NH2:31])\[CH2:29][CH3:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)(=[O:25])=[O:24])=[C:6]([CH2:8][C:9]2[O:10][N:31]=[C:28]([CH2:29][CH3:30])[N:27]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 6007839HCID 6007839, compoundHCID 53234452HCID 53234452, compound

Product 1

HCID 67174408HCID 67174408, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo [c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (0.5 g, 1.4 mmol) and (E)-N′-hydroxypropionimidamide (0.19 mL, 2.1 mmol) in 10 mL of DMF was added EDC (0.5 g, 3.6 mmol) and HOBt (700 mg, 3.6 mmol). The reaction mixture was stirred for 24 hours. After water was added, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound as a yellow solid (6 mg, yield 13%), and cyclized product (7 mg, yield 1%). 4-Amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-((3-ethyl-1,2,4-oxadiazol-5-yl)methyl)benzenesulfonamide: MS calcd for (C18H19BN4O5S): 414.24. MS found (ESI negative): (M−H)−=413.1. 1H NMR (DMSO-d6) δ (ppm): 10.0 (s, 1H), 9.18 (bs, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.41 (s, 1H), 7.22 (d, J=8 Hz, 1H), 7.08 (dd, J=8, 2 Hz, 1H), 6.45 (dd, J=8.8, 2 Hz, 1H, 6.39 (d, J=3 Hz, 1H), 4.86 (s, 2H), 4.48 (s, 2H), 2.63 (q, J=7.6 Hz 2H), 1.17 (t, J=7.6 Hz, 3H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-0e9033fe97de444d8b60b7b076a61469
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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